Estradiol valerate

Estradiol valerate

Systematic (IUPAC) name
(17β)-3-hydroxyestra-1,3,5(10)-trien-17-yl valerate
Clinical data
Routes of administration	Oral, IM[1]
Legal status	℞ (Prescription only)
Identifiers
CAS Number	979-32-8
ATC code	None
PubChem	CID 13791
ChemSpider	13194
Synonyms	17β-Estradiol-17-valerate pentanoate d'estra-1,3,5(10)-triène-3-ol-17β-yle
Chemical data
Formula	C23H32O3
Molar mass	356.498 g/mol
SMILES O=C(O[C@H]3CC[C@H]4[C@H]2[C@@H](c1ccc(O)cc1CC2)CC[C@]34C)CCCC
InChI InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1 Key:RSEPBGGWRJCQGY-RBRWEJTLSA-N

Estradiol valerate (INN, USAN; brand names Altadiol, Deladiol, Delestrogen, Estraval, Progynova, Valergen, many others), or oestradiol valerate (BAN), is a synthetic ester, specifically the 17-pentanoyl ester, of the natural estrogen, 17β-estradiol.^[2][3] It was introduced in the 1950s, and along with estradiol benzoate and estradiol cypionate, has since become one of the most widely used esters of estradiol.^[4]

Upon ingestion, regardless of the route of administration, estradiol valerate behaves as a prodrug, being cleaved by esterases in blood plasma and the liver into 17β-estradiol and valeric acid.^[5][6] However, compared to estradiol itself, estradiol valerate is absorbed more slowly and possesses a longer duration, especially when given in an oil solution via intramuscular injection (in which it acts as a depot). As a result, it can be administered less frequently.^[7][8]

A single intramuscular injection of 4 mg estradiol valerate results in maximal plasma levels of estradiol of about 390 pg/ml within three days of administration, with levels declining to 100 pg/mL by 12–13 days.^[9] A study of high-dose combined administration of 40 mg estradiol valerate and 250 mg hydroxyprogesterone caproate in women once weekly for six months (described as a "pseudopregnancy" regimen) found that serum levels of estradiol increased from 27.8–34.8 pg/mL to 3028–3226 pg/mL after three months and to 2491–2552 pg/mL after six months of treatment.^[10]

See also

• Estrogen ester

References

1. Christoph Zink (1 January 1988). Dictionary of Obstetrics and Gynecology. Walter de Gruyter. p. 86. ISBN 978-3-11-085727-6. Retrieved 20 May 2012.
2. A. D. Roberts (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415. ISBN 978-0-412-27060-4. Retrieved 20 May 2012.
3. Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012.
4. Samuel S. C. Yen (1991). Reproductive endocrinology: physiology, pathophysiology, and clinical management. Saunders. ISBN 978-0-7216-3206-3. Retrieved 20 May 2012.
5. Düsterberg B, Nishino Y (December 1982). "Pharmacokinetic and pharmacological features of oestradiol valerate". Maturitas 4 (4): 315–24. doi:10.1016/0378-5122(82)90064-0. PMID 7169965.
6. "Progynova 1mg (SPC) | Drugs.com" (HTML). Retrieved 2012-09-06.
7. Sriram. Medicinal Chemistry. Pearson Education India. p. 427. ISBN 978-81-317-0031-0. Retrieved 20 May 2012.
8. Oriowo MA, Landgren BM, Stenström B, Diczfalusy E (April 1980). "A comparison of the pharmacokinetic properties of three estradiol esters". Contraception 21 (4): 415–24. doi:10.1016/s0010-7824(80)80018-7. PMID 7389356.
9. M. Notelovitz; P.A. van Keep (6 December 2012). The Climacteric in Perspective: Proceedings of the Fourth International Congress on the Menopause, held at Lake Buena Vista, Florida, October 28–November 2, 1984. Springer Science & Business Media. pp. 399–. ISBN 978-94-009-4145-8.
10. Ulrich U, Pfeifer T, Lauritzen C (1994). "Rapid increase in lumbar spine bone density in osteopenic women by high-dose intramuscular estrogen-progestogen injections. A preliminary report". Horm. Metab. Res. 26 (9): 428–31. doi:10.1055/s-2007-1001723. PMID 7835827.